The Boston Mob Guide: Hit Men, Hoodlums & Hideouts

By Beverly Ford and Stephanie Schorow

Explore the backrooms and seedy hangouts throughout the real story of Boston’s gangster past in this true crime history guide.

The capture of notorious mobster James “Whitey” Bulger closed an infamous chapter in Boston history, yet the city’s criminal underworld has a long and bloody rap sheet that stretches back to the beginning of the twentieth century. Journalists Ford and Schorow reveal the underbelly of Boston through profiles of ruthless gangsters like Charles “King” Solomon, the Angiulo brothers, Joseph “The Animal” Barboza, Stephen “The Rifleman” Flemmi and many more who carried out deadly hits and lucrative heists.

• Language: English
• Publisher: Open Road Integrated Media
• Release date: Mar 12, 2013
• ISBN: 9781614233046

Book preview

INTRODUCTION

On June 22, 2011, the game of Where’s Whitey? ended forever. After sixteen years on the lam, Boston’s most notorious gangster, James J. Whitey Bulger, was captured without incident in Santa Monica, California. The day that many Bostonians thought would never come had arrived, closing an infamous chapter in the city’s history.

The twists and turns of Whitey’s long criminal record—a tale so filled with double-crosses, ironic shifts and colorful characters that it reads like fiction—was a fitting climax to Boston’s long relationship with the dark side. Along with revolutionaries, statesmen, philosophers and authors, Boston has seen a colorful cadre of wise guys, bad boys, criminal masterminds and low-life hoods who have left their mark on the City on the Hill. The book that you now hold in your hand is a guide to these characters and the places they once walked and ruled with intimidation, fear and violence.

And what a crew they are! Anyone not living under a rock in the past year knows that Whitey Bulger was captured, but not everyone knows the full extent of his sordid yet mesmerizing saga, not even longtime Bostonians. Many have heard of Stephen the Rifleman Flemmi, Francis Cadillac Frank Salemme or Joe the Animal Barboza; many don’t know how they got their nicknames or how they are interconnected. And then there are hoodlums whose names are only dimly remembered—men like Steve Wallace and Dodo Walsh of the Gustin gang in South Boston, Joseph Lombardo of the North End or Charles King Solomon, who once presided over the Cocoanut Grove nightclub. There are the Italians: Gennaro Angiulo and his brothers and the Rhode Island–based Patriarca family; the Irish: Buddy McLean and Howie Winter of Somerville; as well as representatives of other immigrant groups and ethnicities. Often, there has been a thin line between legal and illegal businesses. It was not unusual to find Boston families in which one son was a cop and another was a bootlegger, one was a lawyer and the other a thug. Whitey Bulger and his brother, the former Massachusetts senate president William Billy Bulger, are prime examples.

This was the photo flashed around the world in June 2011 when fugitive James Whitey Bulger was arrested at an apartment in Santa Monica, California, where he had been living under the name of Charles Gasko. FBI file photo.

In doing their research, both authors were repeatedly struck by the complicated but strong connections among the various mobsters. Bev, an investigative reporter, had to untangle numerous threads in Whitey’s world, a tough challenge even though she had covered the gangster for years as a cop beat reporter for the Boston Herald. Stephanie found that the names she had encountered while researching the 1942 Cocoanut Grove nightclub and the 1950 Brink’s robbery for her previous books popped up again in the 1950s, 1960s and 1970s. Boston, at its core, is a small town, and the strong connections that once linked Brahmin bluebloods and the literary elite are eerily mirrored by the ties among the hit men, loansharks, guns-for-hire and dope dealers who also walked Boston’s streets.

It’s hard to keep track of them all. There are many good books out there on Boston’s mob landscape; we know—we’ve read a lot of them (see the bibliography), and we relied on the work done over the past fifty years by the ink-stained scribes of the Boston Globe and the Boston Herald, as well as newspapers long gone, such as the Record American. Moreover, not a few of the mobsters mentioned here have published their own memoirs, adding their own perspectives on events. You can read this book on its own or you can refer to it when you read the others; we intend it to be the scorecard to use while getting to know the players.

Because it gets complicated very quickly. There’s the Prohibition period, with bootlegging by Russian Jewish mobster Charles King Solomon and perhaps—as it has been alleged—by the patriarch of the Kennedy clan, Joseph Kennedy. Early Irish gangsters are represented by the South Boston–based Gustin Gang, which ran afoul of the North End Italian mobsters headed by Joseph Lombardo. In the 1950s, the Winter Hill Gang, based in Somerville, emerged, led by, in succession, Buddy McLean, Howie Winter and Bulger. Then there are the battles between the Mullen Gang and the Killeens of South Boston and, in the 1960s, a full-scale mob war among factions from Charlestown, South Boston and Somerville. It’s a dizzying series of hits, revenge slayings and tenuous alliances that are both fascinating and horrifying. Add in the operations of the New England Mafia—the Angiulos of the North End and the Patriarcas of Rhode Island—and you have a thick, uneasy stew of connections, partnerships and animosities. Finally, there’s Whitey, who has connections to nearly all the players here, either as a sometimes partner or deadly rival. Whether you’re new to Boston or have grown up here, Boston Mob Guide: Hit Men, Hoodlums and Hideouts will fill you in on the essentials: what you know, what you don’t know and what you think you know. No one volume could possibly cover every figure—much less every hit—in Boston’s organized crime, but we believe this book is a fair sampling of mob history.

This book was written after we received an offer we couldn’t refuse: The History Press asked us to write a guide to Boston’s gangsters and their hangouts and hits. (At first, the editors wanted a guide to Boston’s mafia, and we had to explain that crime was an equal opportunity employer here for the Irish, Italian, Jews and Chinese.) Because Boston is such a compact city, mobster haunts and hideouts are cheek-by-jowl with other hallmarks of history. Just a stone’s throw from the Old North Church, famed for its one-if-by-land, two-if-by-sea message to Paul Revere, was the Prince Street headquarters of the Angiulo gang. Right on the vaunted Freedom Trail is the North Terminal Garage, the site of the infamous Brink’s heist in 1950. The spectacular ocean views afforded on a walk around Castle Island in South Boston are enjoyed by hundreds of people daily and were once the backdrop for conversations by a strolling Whitey Bulger and his lieutenants, Kevin Weeks and Steve The Rifleman Flemmi. A couple blocks from the hustle of Downtown Crossing is the site of the Blackfriars club, in which five people, including a prominent TV reporter, died in a hail of bullets in 1978 in a case that remains unsolved. Many of the movies about Boston’s bad guys were filmed on location, and in the last chapter, we find the spots where Tinsel Town met The Town.

This book is organized into five chapters. In Chapter 1, we delve into the life of Whitey Bulger. In Chapter 2, we profile the most prominent of the area’s hoodlums. In Chapter 3, we look at local hangouts and hideouts. In Chapter 4, we detail some of the most notorious gangland hits or murders. And in Chapter 5, we look at the Boston mob in the movies.

While we abhor the violence and sorrow these hoodlums brought to their victims, their victims’ families and the city itself, there is an undeniable fascination with how they operated on the far side of the law. Worldwide attention to Bulger’s arrest, which came during our research, only underscores the dark allure. Every city has its underbelly, the dark corners where naughty meets noir, where the law is a moveable feast, not a line in the sand. Few places have an underbelly as colorful—and tragic—as the mean streets of Boston.

Chapter 1

All ROADS LEAD TO WHITEY

JAMES BULGER

Nickname: Whitey

Addresses: 327 West Fourth Street, South Boston;

1012 Third Street, Santa Monica, California

Aliases: Thomas F. Baxter, Tom Harris, Tom Bulger, Mark Shapeton,

Thomas Marshall, Charles Gasko

Born: September 3, 1929, Dorchester, Massachusetts

Association: Winter Hill Gang

The name has been flashed around the country, but just who is James Whitey Bulger? Even before his sensational capture in 2011, his name was legendary both in organized crime circles and on the streets of his hometown, although not quite for the same reason.

To some, James Whitey Bulger was a heartless thug who killed for pleasure. To others, he seemed a beneficent Robin Hood, stealing from the rich, protecting the poor and keeping his South Boston neighborhood free from drugs. To his family, he was the brother of Senator William Billy Bulger, one of the most powerful politicians in Massachusetts history. Whoever he was, James Whitey Bulger was also, at one point, the most wanted man in America, a title he shared with Osama bin Laden, the mastermind behind the September 11, 2001 attacks on the United States.

The road from small-time hoodlum to the FBI’s most wanted was a long one, littered with bodies, payoffs, greed and corruption. It would end, however, on June 22, 2011, in the beachfront community of Santa Monica, California, with the arrest of a frail and elderly Bulger sixteen years after he went on the lam. Bulger had been running from the law all his life, and good luck—and friends in high places—helped him evade arrest for decades.

A mug shot of Whitey Bulger from 1955. Courtesy of the Boston Public Library, Print Department.

From the beginning, Bulger’s life seemed less than charmed. Born to James Joseph Bulger Sr. and Jane McCarthy Bulger on September 3, 1929, in Dorchester, Massachusetts, he was the oldest of six children in a household struggling to make a life in post-Depression Boston. His father, a union laborer and sometimes longshoreman who occasionally worked as a clerk at the Charlestown Navy Yard, lost his arm in an industrial accident when his son was still a boy, sending the family into a spiral of poverty. When he was about nine years old, Bulger’s parents moved the family from the North End into a three-bedroom apartment on Logan Way in the Mary Ellen McCormick Housing Project, a series of brick tenements on the fringes of South Boston, also known as Southie (which is not to be confused with Boston’s South End). The family’s apartment was located just a short distance from Castle Island, a crescent-shaped stretch of beaches and walkways along Boston Harbor that would become one of Bulger’s favorite haunts. In the years to come, he would be photographed there many times by undercover investigators as he walked with mob associates.

A classic mug shot of Whitey Bulger from 1953. Courtesy of the Boston Police Department.

Yet it was a friendship made on the rough-and-tumble streets of South Boston that would forever change the course of Bulger’s life and the lives of many others. It was here that Bulger met John Connolly, a Southie neighbor eleven years his junior who would eventually become his FBI handler. Connolly lived on O’Callahan Way in the Old Colony Housing project and, later, at the Harbor Point Housing project, a short distance away, and his family worshiped at nearby St. Monica’s Church, which the Bulgers also attended.

Whether fact or folklore, Connolly often told a story about how Bulger walked into an ice cream parlor where three eight-year-olds, including a young Connolly, were standing at the counter. Perhaps overcome by generosity, Bulger offered to buy the youngsters each an ice cream cone. Connolly, however, balked, saying that his parents told him never to accept gifts from strangers. According to Connolly, Bulger picked him up, sat him on the counter and said, Hey kid, I’m no stranger. Your mother and father are from Ireland. My mother and father are from Ireland. What kind of ice cream do you want? Reassured, Connolly replied, Vanilla.

As an FBI agent in Boston, Connolly would cite that story as the beginning of his long friendship with the South Boston crime kingpin. It was an admiration that would lead Bulger’s handler down a precipitous path into prison. Yet as a young boy, Connolly looked to Bulger as a childhood hero whose antics, even as a fourteen-year-old, were already drawing the attention of law enforcement. By that age, already a member of a street gang known as the Shamrocks, Bulger was facing a larceny rap. Later charges of robbery, along with assault and battery, helped earn him a stint in a juvenile reformatory.

The Old Colony Housing Development, near where James Whitey Bulger and his brother, the former Massachusetts Senate president, William Bulger, grew up and hung out. This was one of the public housing apartment complexes known as the Southie Projects, where